3,4-dihydro-2H-pyran → 3-(5-chloro-1H-indol-3-yl)propan-1-ol

HRID 925306

反応式

HRID 925306 の反応式
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]N)=[CH:5][CH:4]=1.[O:11]1[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12]1>O.O1CCOCC1.C(OCC)(=O)C>[Cl:2][C:3]1[CH:8]=[C:7]2[C:6](=[CH:5][CH:4]=1)[NH:9][CH:16]=[C:15]2[CH2:14][CH2:13][CH2:12][OH:11]

参加物

6

反応物 2

HCID 80803,4-dihydro-2H-pyranHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)

生成物 1

HCID 199793473-(5-chloro-1H-indol-3-yl)propan-1-ol収率 64.4%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

A mixture of (4-chlorophenyl)hydrazine hydrochloride (5.26 g; 28.50 mmol) and 3,4-dihydro-2H-pyran (2.63 mL; 28.50 mmol) in a mixture of water (9 mL) and dioxane (36 mL) was stirred at 100° C. for 48 hours. After cooling to room temperature the mixture was diluted with ethyl acetate. The aqueous layer was separated and extracted with ethyl acetate. The combined organic layers were dried over magnesium sulphate, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (eluent: 0 to 6% methanol in dichloromethane) to afford 3.85 g (64%) of 3-(5-Chloro-1H-indol-3-yl)propan-1-ol as an oily residue.

後処理

  1. temperatureAfter cooling to room temperature the mixture
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel (eluent: 0 to 6% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-2bbcde54bbd045b79e1190ebcf378597
出典データセット
uspto-grants-2016_03
特許番号
US09284271B2

関連ノート

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